Indeno and naphth[1,2-D]azepines

Abstract

Hydrogenated 1-aminoalkyl-indeno- or naphth[1,2-d]-azepines, e.g. those of the formula ##STR1## Am'=NH 2 , (alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, or benzyl)amino, its N-lower alkyl derivatives; alkyleneimino morpholino or piperazino; R o-3 =H, OH, alkyl, alkoxy, halo or CF 3 ; R 4 ,5 =H or alkyl; X=H 2 or 0; m=1 or 2; q=0 or 1; and salts thereof are potassium-sparing diuretic agents.

I claim: 
     
       1. A compound of the formula ##STR10## wherein pH is unsubstituted 1,2-phenylene, or 1,2-phenylene substituted by up to 3 members selected from lower alkyl, hydroxy, mercapto, lower alkoxy, lower alkylthio, lower alkenyloxy, halogeno and trifluoromethyl; C m  H 2m  is lower alkylene separating the adjacent atoms by one or two carbon atoms; C n  H 2n  is lower alkylene separating the adjacent atoms by two carbon atoms; p is an integer from 1 to 7; Am is amino, simple or mixed, mono- or di-lower (alkyl, alkenyl, alkynyl, hydroxyalkyl, 3 to 7 ring-membered cycloalkyl or H-Ph-alkyl)amino; 5 to 7 ring-membered cycloalkyl or H-ph-alkyl)amino; 5 to 7 ring-membered lower alkyleneimino, morpholino, thiamorpholino, piperazino or N-(lower alkyl or hydroxyalkyl)-piperazino; X represents oxo and R is hydrogen, lower alkyl or hydroxyalkyl; a lower alkanoyl- or 1,11b-dihydro-derivative, or a therapeutically acceptable acid addition salt thereof. 
     
     
       2. A compound as claimed in claim 1, in which formula Ph is 1,2-phenylene, (lower alkyl)-1,2-phenylene, (hydroxy)-1,2-phenylene, mono or di-(lower alkoxy)-1,2-phenylene, (halogeno)-1,2-phenylene or (trifluoromethyl)-1,2-phenylene; C m  H 2m  is methylene, ethylene or 1,2-propylene; C n  H 2n  is ethylene or 1,2-propylene, p is an integer from 1 to 7, Am is amino, lower (alkyl, alkenyl, alkynyl, hydroxyalkyl, 5 or 6 ring-membered cycloalkyl or phenyl-lower alkyl)amino, the N-lower alkyl-derivatives of said sec. amino groups; 5 to 7 ring-membered lower alkyleneimino, morpholino, thiamorpholino, piperazino or N-(lower alkyl or hydroxyalkyl)-piperazino; X represents oxo and R is hydrogen, lower alkyl or hydroxyalkyl; the lower alkanoyl derivatives of said compounds wherein Am is prim. or sec. amino, or both X and R are hydrogen; the 1,11b-dihydro-derivatives, or a therapeutically acceptable acid addition salt thereof. 
     
     
       3. A compound as claimed in claim 1, and corresponding to the formula ##STR11## wherein each of R 0 , R 1 , R 2  and R 3  is hydrogen, or one thereof is alkyl with up to 4 carbon atoms, hydroxy, fluoro, chloro, bromo, or trifluoromethyl; or one or two thereof are alkoxy with up to 4 carbon atoms and the others are hydrogen, Am' is amino, lower (alkyl, alkenyl, alkynyl, hydroxyalkyl, 5 or 6 ring-membered cycloalkyl or benzyl)amino, the N-lower alkyl derivatives of said sec. amino groups, 5 to 7 ring-membered lower alkyleneimino, morpholino, thiamorpholino, piperazino or N-lower alkyl-piperazino; X represents oxo; each of R 4  and R 5  is hydrogen or alkyl with up to 4 carbon atoms; m is the integer 1 or 2 and q is 0 or 1; or a therapeutically acceptable acid addition salt thereof. 
     
     
       4. A compound as claimed in claim 3, in which formula each of R 0 , R 1 , R 2 , and R 3  is hydrogen, or up to two of R 0 , R 1 , R 2  and R 3  are methoxy, or one thereof is methyl, hydroxy, fluoro, chloro or trifluoromethyl and the others are hydrogen; Am' is amino, (methyl, ethyl, n- or i-propyl, allyl, propargyl, 2-hydroxyethyl, cyclopentyl, cyclohexyl or benzyl)amino, or the N-(methyl, ethyl, n- or i-propyl, -butyl, -pentyl, -hexyl or -heptyl)-derivatives of said sec. amino groups, pyrrolidino, piperidino, morpholino or N-methylpiperazino; X is oxo; each of R 4  and R 5  is hydrogen or methyl; m is 2 and q is one; or a therapeutically acceptable acid addition salt thereof. 
     
     
       5. A compound as claimed in claim 3, in which formula each of R 0 , R 1 , R 2  and R 3  is hydrogen, or up to two thereof are methoxy and the others are hydrogen; R 4  is hydrogen; R 5  is methyl; Am' is (methyl, ethyl, n- or i-propyl, allyl or propargyl)amino, or the N-(methyl, ethyl, i-propyl or n-butyl)-derivative thereof, pyrrolidino, piperidino or morpholino; X is oxo, m is two and q is one; or a therapeutically acceptable acid addition salt thereof. 
     
     
       6. A compound as claimed in claim 3 and being the 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, or a therapeutically acceptable acid addition salt thereof. 
     
     
       7. A compound as claimed in claim 3 and being the 1-[2-(N-isopropyl-N-ethylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, or a therapeutically acceptable acid addition salt thereof. 
     
     
       8. A diuretic pharmaceutical composition comprising a diuretically effective amount of a compound as claimed in claim 1, together with a pharmaceutical excipient. 
     
     
       9. A method of traveling edematous conditions in mammals, which comprises administering to said mammals enterally or parenterally a composition as claimed in claim 8.